A stereoselective synthesis of the hexahydroazepine core of (-)-balanol

Tetrahedron Letters

Volumn 47, Issue 10, 2006, Pages 1585-1588

  Raghavan, Sadagopan ^a   Kumar, Ch Naveen ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

( ) Balanol; Bromosulfonamidation; Pummerer ene reaction; Sulfilimine

Indexed keywords

BALANOL; HEXAMETHYLENEIMINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OZONOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 31944444431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.123     Document Type: Article

References (39)

1. P. Kulanthaivel, Y.F. Hallock, C. Boros, S.M. Hamilton, W.P. Janzen, L.M. Ballas, C.R. Loomis, J.B. Jiang, J. Katz, R. Steiner, and J. Clardy J. Am. Chem. Soc. 115 1993 6452
2. S. Ohshima, M. Yanagisawa, A. Katoh, T. Fujii, T. Sano, S. Matsukuma, T. Furumai, M. Fujiu, K. Watanabe, K. Yokose, M. Arisawa, and T. Okuda J. Antibiot. 47 1994 639
3. N. Narayana, T.C. Diller, K. Koide, M.E. Bunnage, K.C. Nicolaou, L.L. Brunton, N.-H. Xuong, L.F. TenEyck, and S.S. Taylor Biochemistry 38 1999 2367
4. J.W. Lampe, P.F. Hughes, C.K. Biggers, S.H. Smith, and H. Hu J. Org. Chem. 59 1994 5147
5. K.C. Nicolaou, M.E. Bunnage, and K. Koide J. Am. Chem. Soc. 116 1994 8402
6. K.C. Nicoalaou, K. Koide, and M.E. Bunnage Chem. Eur. J. 1 1995 454
7. C.P. Adams, S.M. Fairway, C.J. Hardy, D.E. Hibbs, M.B. Hursthouse, A.D. Morley, B.W. Sharp, N. Vicker, and I. Warner J. Chem. Soc., Perkin Trans. 1 1995 2355
8. J.W. Lampe, P.F. Hughes, C.K. Biggers, S.H. Smith, and H. Hu J. Org. Chem. 61 1996 4572
9. P. Barbier, and J. Stadlwieser Chimia 50 1996 530
10. D. Tanner, L. Tedenborg, A. Almario, I. Petersson, I. Csoeregh, N.M. Kelly, P.G. Andersson, and T. Hogberg Tetrahedron 53 1997 4857
11. H. Miyabe, M. Toreida, T. Kiguchi, and T. Naito Synlett 1997 580
12. H. Miyabe, M. Toreida, K. Inoue, K. Tajiri, T. Kiguchi, and T. Naito J. Org. Chem. 63 1998 4397
13. For synthetic approaches to the hexahydroazepine unit, see: A. Muller, D.K. Takyar, S. Wit, and W.A. Konig Liebigs Ann. Chem. 1993 651
14. P.F. Hughes, S.H. Smith, and J.T. Olson J. Org. Chem. 59 1994 5799
15. H. Hu, G.E. Jagdmann, P.F. Hughes, and J.B. Nichols Tetrahedron Lett. 36 1995 3659
16. E. Albertini, A. Barco, S. Benetti, C. DeRisi, G.P. Pollini, and V. Zanirato Synlett 1996 29
17. A.T. Tuch, M. Saniere, Y. LeMerrer, and J.C. Depezay Tetrahedron: Asymmetry 7 1996 2901
18. E. Albertini, A. Barco, S. Benetti, C. De Risi, G.P. Pollini, and V. Zanirato Tetrahedron 53 1997 17177
19. M.H. Wu, and E.N. Jacobsen Tetrahedron Lett. 38 1997 1693
20. E. Coulon, M.C. CanodeAndrade, V. Ratovelomanana-Vidal, and J.P. Genet Tetrahedron Lett. 39 1998 6467
21. C. Herdeis, R.M. Mohareb, R. Neder, F. Schwabenlander, and J. Telser Tetrahedron: Asymmetry 10 1999 4521
22. G.R. Cook, P.S. Shanker, and S.L. Peterson Org. Lett. 1 1999 615
23. A. Furstner, and O.R. Thiel J. Org. Chem. 65 2000 1738
24. D. Riber, R. Hazell, and T. Skrystrup J. Org. Chem. 65 2000 5382
25. C.E. Masse, A.J. Morgan, and J.S. Panek Org. Lett. 2 2000 2571
26. J.P. Genet, P. Phansavath, S.D. Paule, and V. Ratovelomanana-Vidal Eur. J. Org. Chem. 2000 3903
27. J.S. Yadav, and Ch. Srinivas Tetrahedron Lett. 43 2002 3837
28. J.S. Yadav, and Ch. Srinivas Tetrahedron 59 2003 10325
29. S. Raghavan, Ch. Naveen Kumar, K.A. Tony, S. Ramakrishna Reddy, and K. Ravikumar Tetrahedron Lett. 45 2004 7231
30. C. Neagu, and T. Hase Tetrahedron Lett. 34 1993 1629
31. N. Ono, H. Miyake, T. Saito, and A. Kaji Synthesis 1980 952
32. 1H NMR spectral data of the major and minor esters confirmed the 'S' configuration assigned to the major diastereomer 8. The methylene protons appeared upfield and the olefinic protons appeared downfield in the major isomer relative to the minor isomer B.M. Trost, J.L. Belletire, S. Godleski, P.G. McDougal, J.M. Balkovec, J.J. Baldwin, M.E. Christy, G.S. Ponticello, S.L. Varga, and J.P. Springer J. Org. Chem. 51 1986 2370
33. H. Sugihara, R. Tanikaya, and A. Kaji Synthesis 1978 881
34. R. Pummerer Chem. Ber. 42 1909 2282
35. M. Kennedy, and M. McKervey B.M. Trost I. Fleming Comprehensive Organic Chemistry Vol. 7 1991 Pergamon Oxford 193
36. H. Ishibashi, H. Komatsu, and M. Ikeda J. Chem. Res. Synop. 1987 296
37. S. Raghavan, and A. Rajender J. Org. Chem. 68 2003 7094
38. A.L. Gemal, and J.-L. Luche Tetrahedron Lett. 22 1981 4077
39. The HPLC of the mandelate ester of 17 prepared using (S)-(+)-α- methoxyphenylacetic acid revealed the presence of two diastereomers in a 93:7 ratio of the major to minor isomers.